Sodium hydride → 2-{4-[2-(4-Chloro-3-nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazole

HRID 339582Notes

Reaction equation

HRID 339582 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:28]=[CH:27][C:8]2[N:9]=[C:10]([C:12]3[CH:26]=[CH:25][C:15]([CH2:16]P(=O)(OCC)OCC)=[CH:14][CH:13]=3)[S:11][C:7]=2[CH:6]=1.[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][C:31]=1[N+:38]([O-:40])=[O:39]>C1COCC1>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH:34]=[CH:16][C:15]2[CH:14]=[CH:13][C:12]([C:10]3[S:11][C:7]4[CH:6]=[C:5]([O:4][CH3:3])[CH:28]=[CH:27][C:8]=4[N:9]=3)=[CH:26][CH:25]=2)=[CH:32][C:31]=1[N+:38]([O-:40])=[O:39]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 855054-Chloro-3-nitrobenzaldehydeHCID 13599215Diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate

Product 1

HCID 672379852-{4-[2-(4-Chloro-3-nitrophenyl)-vinyl]-phenyl}-6-methoxybenzothiazoleYield 46.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared as described in the Alkene Formation section using sodium hydride (60% dispersion in mineral oil, 0.077 g, 1.92 mmol), diethyl 4-(6-methoxybenzothiazol-2-yl)benzylphosphonate (0.5 g, 1.28 mmol) and 4-chloro-3-nitrobenzaldehyde (0.26 g, 1.41 mmol) in dry THF (20 ml) to give the title compound (0.251 g, 46%) as pale orange needles after work-up and recrystallisation from 1,2-dichloroethane.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0b2f15ff91204b7ca17af982330bed2a
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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